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Hello! Welcome to your first ACen! :)
I would say most everything will have lines of some size, but the only ones you need to make time for are large events like the masquerade, Anime Hell, concerts, etc. These large events will sometimes go over capacity and the excess attendance will need to wait in line until others leave the event. The dances always seem to have overflow lines like this.
Panels will usually have a line, but if you're late getting there, there is still usually room inside. Guest events are the same thing; some will have a packed room and others will have more available seating.
I believe IRT (security) has a rule that you can't line up more than 30 minutes (?) before an event, although it seems to be enforced a little unevenly in the past. I'm not sure if this rule is still in effect this year.
If you are going to Registration on Thursday (for any reason), don't go when it first opens at 4pm. If you go an hour later or so, the initial backup of the line is usually whittled down enough that it's not as long as a wait compared to arriving at 4pm.
That probably doesn't help much, but these are just a few things I thought of.

Not to mention, Facebook's news feed algorithm is changing all the time with the most recent revision giving greater weight to "friends and family." Meaning page posts will be given a lesser priority if they are shown at all. Twitter is also flirting with the the idea of "curated" feeds, making them both useless in that regard because of their unpredictable nature.
Its fine to utilize FB and Twitter, but it is crucial to post the exact same information on the website at the same time.

That's... bizarre.
We were also in the Doubletree since we missed out on the Hyatt (so this was the first time staying there). Our only housekeeping issue (if you could call it that) was on Saturday around noon, a lady from housekeeping staff burst into our room unannounced and without knocking while I was eating some lunch. She started looking in and around everything and when I asked what she was doing, she said she dropped something? After a couple minutes she left without saying anything else, so I'm not sure what that was all about. It just really spooked me, I'm just glad I wasn't changing cosplays at the time.
Our room was cleaned before noon though, so its really strange yours didn't get cleaned at all.

The year that set the bar for me was 2007 when Yasuhiro Nightow (creator of Trigun) was a guest. I was absolutely floored that a con with (at the time) ~13,000 in attendance could get someone like that. I totally understand that getting a guest that everyone will like is not possible, but guests representative of the industries we are celebrating should be a priority.
I agree. I'm not sure what happened this year, but the variety and quantity was lacking.
I was hoping she might be a late addition to the list, but it didn't happen this year.
All of that being said, the Japan Cultural Center stuff was interesting. I'm not sure what I expected exactly but I liked the educational aspect. I was hoping to see the taiko drum demonstration but that was cancelled for some reason.

Right now on Weather Underground, it looks like it will be a little on the cool side with each day a little warmer than the last. Looks like a near zero chance of rain too!
https://www.wunderground.com/cgi-bin/findweather/getForecast?query=Rosemont%2C+IL
Friday 05/20
0 % Precip. / 0 in
Partly cloudy. High 68F. Winds ENE at 10 to 15 mph.
Friday Night
0 % Precip. / 0 in
A few clouds. Low 49F. Winds NNE at 5 to 10 mph.
Saturday 05/21
0 % Precip. / 0 in
Partly cloudy. High around 70F. Winds NNE at 10 to 15 mph.
Saturday Night
0 % Precip. / 0 in
A mostly clear sky. Low around 50F. Winds NW at 5 to 10 mph.
Sunday 05/22
0 % Precip. / 0 in
Sunny skies. High 74F. Winds NE at 5 to 10 mph.

Its still a little far out to say for sure what the exact weather is going to be (forecasts start to be reliable about 3 days before), but the Climate Prediction Office seems to show trends towards normal temps and slightly above average precip. I do like looking at the different forecasts like Accuweather's though, its fun to think about what this year might hold.
Also just for fun, the Old Farmers Almanac is calling for cool temps that transition to normal/nice. :)
Around 8 days out is when there will start to be "real" forecasts with some level of reliability, so around Thursday.

This was mentioned at one point on the 2015 panelist mailing list:
I'm not sure if 2016 would be any different since the panel rooms are all in the same area. Email the department head for clarification.